US20210360949A1 - Beverage, method for producing beverage, or combination for beverage - Google Patents

Beverage, method for producing beverage, or combination for beverage Download PDF

Info

Publication number
US20210360949A1
US20210360949A1 US17/057,424 US201917057424A US2021360949A1 US 20210360949 A1 US20210360949 A1 US 20210360949A1 US 201917057424 A US201917057424 A US 201917057424A US 2021360949 A1 US2021360949 A1 US 2021360949A1
Authority
US
United States
Prior art keywords
salt
amino acid
pyrroloquinoline quinone
beverage
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
US17/057,424
Other languages
English (en)
Inventor
Kazuto Ikemoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Gas Chemical Co Inc
Original Assignee
Mitsubishi Gas Chemical Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Assigned to MITSUBISHI GAS CHEMICAL COMPANY, INC. reassignment MITSUBISHI GAS CHEMICAL COMPANY, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: IKEMOTO, KAZUTO
Publication of US20210360949A1 publication Critical patent/US20210360949A1/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/66—Proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/03—Organic compounds
    • A23L29/045—Organic compounds containing nitrogen as heteroatom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3544—Organic compounds containing hetero rings
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to a beverage in which pyrroloquinoline quinone, an amino acid and/or a salt thereof, and ascorbic acid and/or a salt thereof are blended, and a method for producing the same.
  • Non-alcoholic beverages also called soft drinks
  • soft drinks are taken habitually as convenient means of hydration, and besides, such beverages give pleasure to consumers having varieties of fondness and needs by flavors and functions rich in variety.
  • amino acids having a branched bulky substituent called BCCA (Branched Chain Amino Acids) are blended in many sports drinks on the assumption of having an effect on fatigue recovery.
  • BCCA Branched Chain Amino Acids
  • taste improvement there is extensively carried out blending of amino acids to green tea and black tea beverages. For example, by blending an amino acid having umami taste, typified by theanine, palatability is enhanced more.
  • pyrroloquinoline quinone has functionalities including cerebral function improvement, blood sugar level improvement, antioxidation, and life extension. Further, pyrroloquinoline quinone also has a mitochondorion-activating function and is expected to be blended in sports beverages.
  • Patent Literature 1 Japanese Patent Laid-Open No. 2010-132599
  • Patent Literature 2 Japanese Patent Laid-Open No. 2017-175966
  • Patent Literature 3 Japanese Patent Laid-Open No. 2011-024476
  • Patent Literature 4 Japanese Patent Laid-Open No. 9-70296
  • Non Patent Literature 1 J. Am. Chem. Soc., 1995, 117, 3278-3279
  • pyrroloquinoline quinone has an effect of increasing the nerve growth factor by being combined with an amino acid, particularly glycine, L-serine or L-tryptophan (Patent Literature 1). For such a reason, beverages are desired in which a combination of an amino acid and pyrroloquinoline quinone is blended.
  • Patent Literature 2 black tea-like beverage
  • Patent Literature 3 an alcoholic beverage
  • the present inventor has found a phenomenon of acceleratedly generating odors originated from BCAA in a beverage in which the BCAA and pyrroloquinoline quinone are mixed, but no solution thereto is known.
  • the problem to be solved by the present invention is to lessen the decrease of pyrroloquinoline quinone due to an amino acid in a beverage containing the amino acid and the pyrroloquinoline quinone, and the like.
  • the present inventor has surprisingly found that by incorporating ascorbic acid (vitamin C) in a beverage containing an amino acid and pyrroloquinoline quinone, the decrease of the content of pyrroloquinoline quinone is suppressed. It has further been found that by blending the amino acid after ascorbic acid is mixed with pyrroloquinoline quinone in advance, the decrease of pyrroloquinoline quinone can be more effectively suppressed. It has further been found that ascorbic acid has also an effect of suppressing odors of BCAA.
  • the present invention includes the following aspects, but is not limited thereto.
  • a beverage comprising pyrroloquinoline quinone and/or a salt thereof; an amino acid and/or a salt thereof; and ascorbic acid and/or a salt thereof, wherein a content of ascorbic acid and/or a salt thereof is two or more mass times a content of pyrroloquinoline quinone and/or a salt thereof.
  • amino acid comprises at least one of non-essential amino acids, branched chain amino acids and free amino acids.
  • a combination comprising a mixture comprising pyrroloquinoline quinone and/or a salt thereof and ascorbic acid and/or a salt thereof in the content two or more mass times a content of pyrroloquinoline quinone and/or a salt thereof; and an amino acid and/or a salt thereof.
  • the blending ascorbic acid and/or a salt thereof enables to provide a beverage in which the content of pyrroloquinoline quinone is retained even while the beverage contains an amino acid and/or a salt thereof.
  • the amino acid contained in the beverage is a branched chain amino acid
  • its intrinsic odor can also be suppressed by ascorbic acid and/or a salt thereof.
  • the beverage according to the present invention is characterized in blending ascorbic acid and/or a salt thereof (hereinafter, referred to also simply as “ascorbic acid”) into a combination of pyrroloquinoline quinone and/or a salt thereof (hereinafter, referred to also simply as “pyrroloquinoline quinone”) and an amino acid and/or a salt thereof (hereinafter, referred to also simply as “amino acid”).
  • ascorbic acid a combination of pyrroloquinoline quinone and/or a salt thereof
  • amino acid and/or a salt thereof hereinafter, referred to also simply as “amino acid”.
  • Pyrroloquinoline quinone to be used as a raw material of the beverage according to the present invention is a substance having a structure represented by formula 1.
  • the substance may be present as a free form of pyrroloquinoline quinone, or may be present as a salt thereof.
  • Pyrroloquinoline quinone and/or a salt thereof to be used may be a commercially available one, or can also be produced by a well-known method.
  • the salt of pyrroloquinoline quinone to be used in the present invention includes alkaline metal salts, alkaline earth metal salts and ammonium salts thereof, but is preferably an alkaline metal salt thereof.
  • the alkaline metal salt of pyrroloquinoline quinone to be used in the present invention includes salts of sodium, potassium, lithium, cesium, rubidium, and the like. In the point of easy availability, a sodium salt and a potassium salt as the alkaline metal salt are more preferable.
  • the alkaline metal salt of pyrroloquinoline quinone may be an alkaline metal salt which is obtained by substitution with one to three alkaline metal atoms, and may be any of a monoalkaline metal salt, a dialkaline metal salt and a trialkaline metal salt. Preferable is a dialkaline metal salt. A disodium salt and a dipotassium salt are especially preferable.
  • Ascorbic acid may be in a form of a salt such as sodium ascorbate or a calcium ascorbate.
  • An ascorbic acid salt is preferably sodium ascorbate, which makes pyrroloquinoline quinone to be hardly deposited in a solution.
  • Pyrroloquinoline quinone and/or a salt thereof by being mixed with ascorbic acid, may partially or wholly form a reduced-type pyrroloquinoline quinone and/or a salt thereof in the beverage.
  • the reduced-type pyrroloquinoline quinone has a structure represented by the following formula 2.
  • the oxidized-type pyrroloquinoline quinone and/or a salt thereof and the reduced-type pyrroloquinoline quinone and/or a salt thereof, since being easily reduced and oxidized, can be considered to be equivalent; therefore, in the case of referring to the concentration in the beverage, description will be made without distinction between the both.
  • the reduced-type pyrroloquinoline quinone is easily oxidized by oxygen in the air.
  • the contents of pyrroloquinoline quinone and an amino acid in the beverage can suitably be determined by those skilled in the art according to a desired effect.
  • the content of pyrroloquinoline quinone and/or a salt thereof in the present invention is 10 to 400 mg/L.
  • a preferable content is 10 to 100 mg/L.
  • the content of an amino acid is 0.1 mg to 25 g/L.
  • the content of ascorbic acid and/or a salt thereof is two or more mass times the content of pyrroloquinoline quinone and/or a salt thereof, and may also be, for example, 2.5 or more mass times, 5 or more mass times, 10 or more mass times, or 20 or more mass times.
  • a larger amount of ascorbic acid and/or a salt thereof gives a larger effect of suppressing the decrease of the content of pyrroloquinoline quinone, and the maximum amount of ascorbic acid which can be used is 300 mass times the amount of pyrroloquinoline quinone and/or a salt thereof.
  • the content of ascorbic acid is 30 to 120,000 mg/L, and preferably 1,000 to 10,000 mg/L.
  • the amino acid to be used in the present invention is not especially limited, and any amino acid can be selected.
  • any amino acid can be selected.
  • essential amino acids selected from the group consisting of histidine, isoleucine, leucine, lysine, methionine, phenylalanine, threonine, tryptophan and valine; non-essential amino acids selected from the group consisting of glycine, asparagine, aspartic acid, alanine, arginine, cysteine, glutamine, glutamic acid, proline, serine and tyrosine; and free amino acids selected from the group consisting of theanine, ornithine, citrulline and taurine.
  • the content of the amino acid is preferably 0.1 mg to 25 g/L, more preferably 50 mg to 1,500 mg/L, and still more preferably 100 mg to 1,200 mg/L.
  • branched chain amino acids such as valine, leucine and isoleucine are preferable.
  • non-essential amino acids glycine is preferable.
  • free amino acids theanine and ornithine are preferable.
  • the salt of the amino acid is not especially limited, but examples thereof for acidic groups such as a carboxy group include salts with an alkaline metal such as sodium or potassium, salts with an alkaline earth metal such as calcium or magnesium, ammonium salts, aluminum salts, zinc salts, salts with an organic amine such as triethylamine, ethanolamine, morpholine, pyrrolidine, piperidine, piperazine or dicyclohexylamine, and salts with a basic amino acid such as arginine or lysine.
  • an alkaline metal such as sodium or potassium
  • salts with an alkaline earth metal such as calcium or magnesium
  • ammonium salts aluminum salts
  • zinc salts salts with an organic amine such as triethylamine, ethanolamine, morpholine, pyrrolidine, piperidine, piperazine or dicyclohexylamine
  • salts with a basic amino acid such as arginine or lysine.
  • Examples thereof for basic groups such as an amino group include salts with an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid or hydrobromic acid, salts with an organic carboxylic acid such as acetic acid, citric acid, benzoic acid, maleic acid, fumaric acid, tartaric acid, succinic acid, tannic acid, butyric acid, hibenzic acid, pamoic acid, enanthic acid, decanoic acid, teoclic acid, salicylic acid, lactic acid, oxalic acid, mandelic acid or malic acid, and salts with an organic sulfonic acid such as methanesulfonic acid, benzenesulfonic acid or p-toluenesulfonic acid.
  • an organic carboxylic acid such as acetic acid, citric acid, benzoic acid, maleic acid, fumaric acid, tartaric acid, succinic acid, tannic acid,
  • the present invention provides a beverage having functions of both of pyrroloquinoline quinone and the amino acid.
  • the present inventor has found that the mixing of pyrroloquinoline quinone and/or a salt thereof in the beverage makes generation of the odors easier.
  • the blending of ascorbic acid leads to lowering the reactivity of pyrroloquinoline quinone with the branched chain amino acid and is thereby effective also for suppression of the odor generation.
  • the beverage according to the present invention can be used at a pH of 1 to 9.
  • a refreshing feeling is often given by making the pH acidic, and the pH can be adjusted preferably to 1 to 4, and more preferably to 2.5 to 5.5.
  • an amino acid is further blended in such sports beverages, and it is conceivable that the present invention is especially suitable for such sports beverages.
  • a substance to be used for adjustment of pH is not especially limited as long as being a substance which can be added to food.
  • the ascorbic acid functions also as a reducing agent, and can be used also as a pH adjustor. Then, by adding the alkaline metal salt, a buffer effect is exhibited and the pH can be made not to vary.
  • ascorbic acid citric acid, sodium ascorbate or sodium citrate
  • citric acid sodium ascorbate or sodium citrate
  • an amino acid is mixed after an elapse of a predetermined period after their mixing, for example, after an elapse of 20 min or more thereafter.
  • a reducing agent is mixed after an amino acid and/or a salt thereof and pyrroloquinoline quinone and/or a salt thereof are mixed, the effect cannot be attained.
  • a mixture containing pyrroloquinoline quinone and/or a salt thereof and ascorbic acid and/or a salt thereof in the content two or more mass times the content of pyrroloquinoline quinone and/or a salt thereof can be used as a raw material for production of the beverage.
  • stable production can be made.
  • additives commonly used for beverages can be blended unless such additives inhibit intended effects.
  • additives include sweeteners, acidulants, preservatives, coloring matters and antioxidants.
  • food components such as fruits juice, coffee extracts, tea leaf extracts and milk components may be added.
  • a sweetener may be blended according to flavor of a beverage of interest.
  • the exemplary type of the sweetener to be blended includes monosaccharides, disaccharides, isomerized sugar, oligosaccharides, polysaccharides, sugar alcohols, starch syrup and artificial sweeteners, but is not especially limited as long as being allowed to use as a sweetener for food and drink.
  • the monosaccharide specifically includes glyceraldehyde, threose, arabinose, xylose, ribose, ribulose, xylulose, glucose, mannose, galactose, tagatose, allose, altose, gulose, idose, talose, sorbose, psicose and fructose.
  • the disaccharide includes trehalose, sucrose and lactose.
  • the oligosaccharide includes maltotriose, raffinose and cyclodextrin.
  • cyclodextrin is preferable because it enhances the effect of suppressing the decomposition of pyrroloquinoline quinone by ascorbic acid.
  • the polysaccharide includes starch syrup and hydrogenated starch syrup.
  • the sugar alcohol includes threitol, erythritol, adonitol, arabitol, xylitol, talitol, sorbitol, mannitol, iditol, dulcitol and inositol.
  • the artificial sweetener includes saccharin, aspartame, acesulfame potassium and sucralose. Among these, acesulfame potassium and sorbitol are preferable.
  • the beverage according to the present invention can be made into a carbonated beverage.
  • Carbonic acid may be blended after a beverage is prepared.
  • the beverage according to the present invention includes soft drinks defined in the notification based on the Food Sanitation Act (Japan).
  • the form of the beverage according to the present invention is not especially limited as long as being a beverage containing an amino acid, but examples thereof include sports beverages, fruit beverages, tea beverages, coffee beverages, milky beverages, carbonated beverages, functional beverages and energy drinks. Among these, sports beverages are preferable.
  • the beverage according to the present invention can be packaged in a container.
  • the form of the container is not limited, and the beverage can be made into a packaged beverage by filling a sealed container such as a bottle, a can or a pet bottle with the beverage.
  • the present invention provides a method for producing the beverage, the method comprising a step of mixing pyrroloquinoline quinone and/or a salt thereof with ascorbic acid and/or a salt thereof in the content two or more mass times the content of pyrroloquinoline quinone and/or a salt thereof, and thereafter mixing an amino acid and/or a salt thereof.
  • the amino acid is mixed after an elapse of a predetermined period, preferably an elapse of 20 to 70 min or longer, more preferably 30 to 60 min or longer from the mixing of pyrroloquinoline quinone with ascorbic acid.
  • a reducing agent is mixed after an elapse of a predetermined period from mixing of an amino acid and/or a salt thereof with pyrroloquinoline quinone and/or a salt thereof, the effect may not be attained in some cases.
  • the contact of pyrroloquinoline quinone with an amino acid is carried out in a solution, and the temperature in this case is ⁇ 10° C. to 120° C., preferably 10° C. to 90° C., and more preferably at room temperature, for example, at about 20° C. to 25° C., at which this procedure can easily be carried out.
  • other components can be added simultaneously with the mixing of pyrroloquinoline quinone and/or a salt thereof with ascorbic acid and/or a salt thereof, or the amino acid and other components can be added to the resulting mixture of pyrroloquinoline quinone and/or a salt thereof with ascorbic acid and/or a salt thereof after an elapse of a predetermined period, for example, after the contact for 20 min or longer.
  • the resultant is subjected to a sterilization step and a bottle-filling step to thereby complete a packaged beverage.
  • heat sterilization or filter sterilization can be used.
  • the heat sterilization may be carried out under the conditions of 90° C. or higher and 30 sec or longer.
  • the sterilization is carried out according to needs and can be used without restriction on the conditions.
  • the present invention provides a combination of a mixture containing pyrroloquinoline quinone and/or a salt thereof and ascorbic acid and/or a salt thereof in the content two or more mass times the content of pyrroloquinoline quinone and/or a salt thereof; and an amino acid.
  • the beverage production can be carried out with pyrroloquinoline quinone in a stable state.
  • BioPQQ Registered Trademark
  • Mitsubishi Gas Chemical Co., Ltd. was used.
  • Other reagents used were reagents manufactured by Wako Pure Chemical Industries, Ltd.
  • aqueous solution was prepared so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L and the concentration of glycine became 100 mg/L.
  • the resulting aqueous solution was stored at 30° C. for five days, and subjected to an HPLC analysis; the result was: 77% of PQQ changed to IPQ.
  • An aqueous solution was prepared so that the concentration of the pyrroloquinoline quinone disodium salt became 400 mg/L and the concentration of ascorbic acid became 10 g/L.
  • the resulting aqueous solution was stored at room temperature (25° C.) for one day.
  • the resultant aqueous solution was diluted with water so that the concentration of pyrroloquinoline quinone disodium salt became 40 mg/L and the concentration of ascorbic acid became 1 g/L, and glycine was added thereto so as to become a concentration of 100 mg/L to thereby obtain an aqueous solution, which was then stored at 30° C. for five days.
  • An aqueous solution was prepared so that the concentration of the pyrroloquinoline quinone disodium salt became 400 mg/L and the concentration of ascorbic acid became 5 g/L.
  • the resulting aqueous solution was stored at room temperature (25° C.) for one day.
  • the resultant aqueous solution was diluted with water so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L and the concentration of the ascorbic acid became 0.5 g/L, and glycine was added thereto so as to have a concentration of 100 mg/L to thereby obtain an aqueous solution, which was then stored at 30° C. for five days.
  • An aqueous solution was prepared so that the concentration of the pyrroloquinoline quinone disodium salt became 400 mg/L and the concentration of ascorbic acid became 1 g/L.
  • the resulting aqueous solution was stored at room temperature (25° C.) for one day.
  • the resultant aqueous solution was diluted with water so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L and the concentration of ascorbic acid became 100 mg/L., and glycine and citric acid were added thereto so as to have concentrations of 100 mg/L and 2 g/L, respectively, to thereby obtain an aqueous solution, which was then stored at 30° C. for five days.
  • aqueous solution was prepared so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L; the concentration of valine became 500 mg/L; the concentration of leucine became 500 mg/L; and the concentration of isoleucine became 500 mg/L.
  • the pH during the preparation was 5.3.
  • the resulting aqueous solution was stored at 50° C. for two days, and thereafter subjected to an HPLC analysis; the result was that pyrroloquinoline quinone having changed to IPQ accounted for 51% and pyrroloquinoline quinone accounted for 49%.
  • aqueous solution was prepared so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L; the concentration of ascorbic acid became 1 g/L; the concentration of valine became 500 mg/L; the concentration of leucine became 500 mg/L; and the concentration of isoleucine became 500 mg/L.
  • the pH during the preparation was 3.6.
  • the resulting aqueous solution was stored at 50° C. for two days, and thereafter subjected to an HPLC analysis; the result was that pyrroloquinoline quinone having changed to IPQ accounted for 0%.
  • the reaction from pyrroloquinoline quinone to IPQ by amino acids including also BCAA did not occur. Odors caused by branched chain amino acids were not generated.
  • aqueous solution was prepared so that the components of raw material had the following concentrations. In the case of mixing pyrroloquinoline quinone disodium salt and ascorbic acid together, 30 min after the mixing of the both, other components were mixed. The resulting aqueous solution was stored at 50° C. for four days, and thereafter subjected to an HPLC analysis to measure the recovery of the pyrroloquinoline quinone disodium salt.
  • An aqueous solution was prepared so that components of raw material had the following concentrations.
  • the preparation was carried out by mixing the both and 30 min after the mixing, mixing other materials.
  • 100 ml of the resulting aqueous solution was put in a 110-ml glass container, and stored at 50° C. for three days. After the container was returned to room temperature, odor was smelled. Further the aqueous solution was subjected to an HPLC analysis to measure the recovery of the pyrroloquinoline quinone disodium salt.
  • Examples 7 and 8 could protect PQQ and also suppress odor.
  • aqueous solution was prepared so that pyrroloquinoline quinone disodium salt was contained at 40 mg/L; ascorbic acid at 1 g/L; citric acid at 1,200 mg/L; sodium citrate at 100 mg/L; valine at 40 mg/L; leucine at 100 mg/L; isoleucine at 40 mg/L; and fructose at 50 g/L.
  • pyrroloquinoline quinone disodium salt was contained at 40 mg/L; ascorbic acid at 1 g/L; citric acid at 1,200 mg/L; sodium citrate at 100 mg/L; valine at 40 mg/L; leucine at 100 mg/L; isoleucine at 40 mg/L; and fructose at 50 g/L.
  • the other materials were mixed.
  • the pH during the mixing was 3.0.
  • the resulting aqueous solution was stored at 50° C.
  • aqueous solution was prepared so that pyrroloquinoline quinone disodium salt was contained at 40 mg/L; citric acid at 1,200 mg/L; sodium citrate at 100 mg/L; valine at 40 mg/L; leucine at 100 mg/L; isoleucine at 40 mg/L; and fructose at 50 g/L.
  • the pH during the preparation was 3.0.
  • the resulting aqueous solution was stored at 50° C. for three days, and thereafter subjected to an HPLC analysis to determine the content of PQQ; the result was that the recovery of PQQ was 25%. In the case where ascorbic acid was not present, PQQ was not sufficiently recovered and the stability of PQQ in the beverage was lost.
  • the resulting beverage was stored at 50° C. for three days, and subjected to an HPLC analysis to determine the content of PQQ; the result was that the recovery of PQQ was 97%.
  • the resulting beverage was stored at 50° C. for three days, and subjected to an HPLC analysis to determine the content of PQQ; the result was that the recovery of PQQ was 95%.
  • the resulting beverage was stored at 50° C. for three days, and subjected to an HPLC analysis to determine the content of PQQ; the result was that the recovery of PQQ was 91%.
  • An aqueous solution (pH: 6.4) was prepared by simultaneously adding components so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L and the concentration of theanine became 400 mg/L.
  • the resulting aqueous solution was stored at 60° C. for seven days, and then subjected to an HPLC measurement; the result was that the recovery of PQQ was 29%.
  • An aqueous solution (pH: 2.6) was prepared by simultaneously adding components so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L; the concentration of ascorbic acid, 2,000 mg/L; the concentration of citric acid, 3,000 mg/L; the concentration of theanine, 400 mg/L; and the concentration of ⁇ -cyclodextrin, 5,000 mg/L.
  • the resulting aqueous solution was stored at 60° C. for seven days, and then subjected to an HPLC measurement; the result was that the recovery of PQQ was 100%.
  • An aqueous solution (pH: 2.7) was prepared by simultaneously adding components so that the pyrroloquinoline quinone disodium salt was contained at 40 mg/L; ascorbic acid at 2,000 mg/L; citric acid at 3,000 mg/L; theanine at 400 mg/L; ⁇ -cyclodextrin at 5,000 mg/L; and an isomerized sugar at 50 g/L.
  • the isomerized sugar used was an isomerized sugar (fructose content: 55% or higher) (hereinafter, the same) of Oji Cornstarch Co., Ltd.
  • the resulting aqueous solution was stored at 60° C. for seven days, and then subjected to an HPLC measurement; the result was that the recovery of PQQ was 96%.
  • An aqueous solution (pH: 7.5) was prepared by simultaneously adding components so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L and the concentration of ornithine became 400 mg/L.
  • the resulting aqueous solution was stored at 60° C. for seven days. The recovery of PQQ on an HPLC was 29%.
  • An aqueous solution (pH: 2.5) was prepared by simultaneously adding components so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L; the concentration of ascorbic acid, 2,000 mg/L; the concentration of citric acid, 3,000 mg/L; the concentration of ornithine, 400 mg/L; and the concentration of y-cyclodextrin, 5,000 mg/L.
  • the resulting aqueous solution was stored at 60° C. for seven days, and then subjected to an HPLC measurement; the result was that the recovery of PQQ was 100%.
  • An aqueous solution (pH: 2.7) was prepared by simultaneously adding components so that the concentration of the pyrroloquinoline quinone disodium salt became 40 mg/L; the concentration of ascorbic acid, 2,000 mg/L; the concentration of citric acid, 3,000 mg/L; the concentration of ornithine, 400 mg/L; the concentration of ⁇ -cyclodextrin, 5,000 mg/L; and the concentration of the isomerized sugar, 50 g/L.
  • the resulting aqueous solution was stored at 60° C. for seven days, and then subjected to an HPLC measurement; the result was: the recovery of PQQ was 98%.
  • a beverage which retains the content of pyrroloquinoline quinone while containing an amino acid, can be provided.
  • the amino acid is a branched chain amino acid, its intrinsic odor is also suppressed by ascorbic acid.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Tea And Coffee (AREA)
US17/057,424 2018-06-05 2019-05-28 Beverage, method for producing beverage, or combination for beverage Pending US20210360949A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2018-107822 2018-06-05
JP2018107822 2018-06-05
PCT/JP2019/021157 WO2019235306A1 (ja) 2018-06-05 2019-05-28 飲料、飲料の製造方法又は組み合わせ

Publications (1)

Publication Number Publication Date
US20210360949A1 true US20210360949A1 (en) 2021-11-25

Family

ID=68769868

Family Applications (1)

Application Number Title Priority Date Filing Date
US17/057,424 Pending US20210360949A1 (en) 2018-06-05 2019-05-28 Beverage, method for producing beverage, or combination for beverage

Country Status (5)

Country Link
US (1) US20210360949A1 (zh)
EP (1) EP3777554A4 (zh)
JP (1) JP7327395B2 (zh)
TW (1) TWI818031B (zh)
WO (1) WO2019235306A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210267240A1 (en) * 2018-08-30 2021-09-02 Mitsubishi Gas Chemical Company, Inc. Photodeterioration inhibitor, beverage comprising the same, and method for inhibiting photodeterioration

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7532829B2 (ja) 2020-03-19 2024-08-14 三菱瓦斯化学株式会社 ピロロキノリンキノンの安定化方法、並びに、コーヒー及び紅茶
CN115211567A (zh) * 2022-07-12 2022-10-21 重庆师范大学 银耳多糖吡咯喹啉醌口服液及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140023771A1 (en) * 2005-11-23 2014-01-23 The Coca-Cola Company High-potency sweetener composition with phytosterol and compositions sweetened therewith
US20150182579A1 (en) * 2012-07-05 2015-07-02 N.V. Nutricia Dietary Fibre for Use in the Treatment of a Gastro-Intestinal Side-Effect of a Nutrition or Medicament

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3731614B2 (ja) 1995-09-05 2006-01-05 三菱瓦斯化学株式会社 イミダゾピロロキノリン類の製造法
US8017147B2 (en) * 2008-04-07 2011-09-13 Mazed Mohammad A Nutritional supplement for the prevention of cardiovascular disease, alzheimer's disease, diabetes, and regulation and reduction of blood sugar and insulin resistance
US9823737B2 (en) * 2008-04-07 2017-11-21 Mohammad A Mazed Augmented reality personal assistant apparatus
JP2010132599A (ja) 2008-12-04 2010-06-17 Mitsubishi Gas Chemical Co Inc 脳機能改善用組成物
JP2011024476A (ja) 2009-07-24 2011-02-10 Mitsubishi Gas Chemical Co Inc ピロロキノリンキノン含有アルコール
WO2011102387A1 (ja) * 2010-02-16 2011-08-25 三菱瓦斯化学株式会社 還元型ピロロキノリンキノンの製造方法
JP5803150B2 (ja) * 2011-03-02 2015-11-04 三菱瓦斯化学株式会社 ピロロキノリンキノンーシクロデキストリン包接体
CN107106554A (zh) * 2014-09-22 2017-08-29 国立大学法人名古屋大学 新型寿命延长剂、使用该寿命延长剂的寿命延长方法、新型双氧化酶活化剂、双氧化酶活化剂的活化方法、寿命延长剂的制造、以及双氧化酶活化剂的制造
JP2017175966A (ja) 2016-03-29 2017-10-05 三菱瓦斯化学株式会社 ピロロキノリンキノン含有紅茶風飲料
JP7276137B2 (ja) * 2017-10-25 2023-05-18 三菱瓦斯化学株式会社 ピロロキノリンキノン含有酸性飲料及びピロロキノリンキノンの析出抑制方法
WO2019138817A1 (ja) * 2018-01-12 2019-07-18 三菱瓦斯化学株式会社 分析方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140023771A1 (en) * 2005-11-23 2014-01-23 The Coca-Cola Company High-potency sweetener composition with phytosterol and compositions sweetened therewith
US20150182579A1 (en) * 2012-07-05 2015-07-02 N.V. Nutricia Dietary Fibre for Use in the Treatment of a Gastro-Intestinal Side-Effect of a Nutrition or Medicament

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
English Translation of WO2011102387 by google C07D471/04; 3-2016 *
English Translation of WO2016047637 by google C07D471/04; 9-2015 *
Nakano, M., Murayama, Y., Hu, L., Ikemoto, K., Uetake, T., Sakatani, K. (2016). Effects of Antioxidant Supplements (BioPQQ™) on Cerebral Blood Flow and Oxygen Metabolism in the Prefrontal Cortex. In: Luo, Q., Li, L., Harrison, D., Shi, H., Bruley, D. (eds) Oxygen Transport to Tissue XXXVIII. Advances in Experiment *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210267240A1 (en) * 2018-08-30 2021-09-02 Mitsubishi Gas Chemical Company, Inc. Photodeterioration inhibitor, beverage comprising the same, and method for inhibiting photodeterioration

Also Published As

Publication number Publication date
JPWO2019235306A1 (ja) 2021-06-17
TWI818031B (zh) 2023-10-11
JP7327395B2 (ja) 2023-08-16
EP3777554A4 (en) 2022-01-05
TW202015539A (zh) 2020-05-01
WO2019235306A1 (ja) 2019-12-12
EP3777554A1 (en) 2021-02-17

Similar Documents

Publication Publication Date Title
US20210360949A1 (en) Beverage, method for producing beverage, or combination for beverage
JP5314207B1 (ja) ミネラル含有飲料及びその製造方法、並びにミネラル含有飲料の塩味抑制方法
CN113710105A (zh) 甜菊醇糖苷溶解度增强剂
JP5955358B2 (ja) シトルリン含有飲料
EP3111775B1 (en) Carbonated beverage containing high-intensity sweetener
WO2008059609A1 (en) Beverage packed in container
JP5223026B2 (ja) 容器詰飲料
JP2017175966A (ja) ピロロキノリンキノン含有紅茶風飲料
US20080175970A1 (en) Amino acid-containing acidic beverage and a method for manufacturing the same
JP2015006167A (ja) 炭酸飲料
JP2015006168A (ja) 炭酸飲料
JP7377442B2 (ja) ピロロキノリンキノンの安定化剤及び安定化方法
JP2016158585A (ja) アルコール飲料、及びアルコール飲料の香味改善方法
JP7532829B2 (ja) ピロロキノリンキノンの安定化方法、並びに、コーヒー及び紅茶
JP2016158624A (ja) アルコール飲料、及びアルコール飲料の香味改善方法
US20220295847A1 (en) Method for producing aqueous composition containing rebaudioside d, sweetening composition containing rebaudioside d, and beverage containing sweetening composition
EP4454481A2 (en) Method for producing aqueous composition containing rebaudioside d, sweetening composition containing rebaudioside d, and beverage containing sweetening composition
CN118541034A (zh) 碳酸饮料及增强碳酸饮料的碳酸感的方法
CN114845567A (zh) 高溶解性瑞鲍迪苷d复合体
JP2019076045A (ja) フルーティーなノンアルコールビール
JPH1160486A (ja) チアミン類配合液剤

Legal Events

Date Code Title Description
AS Assignment

Owner name: MITSUBISHI GAS CHEMICAL COMPANY, INC., JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:IKEMOTO, KAZUTO;REEL/FRAME:055233/0668

Effective date: 20201211

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED